US1955766A - Manufacture of sulphonated oils - Google Patents

Manufacture of sulphonated oils Download PDF

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US1955766A
US1955766A US572225A US57222531A US1955766A US 1955766 A US1955766 A US 1955766A US 572225 A US572225 A US 572225A US 57222531 A US57222531 A US 57222531A US 1955766 A US1955766 A US 1955766A
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oil
sulphonated
oils
sulphonation
sulphuric acid
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US572225A
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Pohl Edward
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SELMA POHL
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SELMA POHL
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/03—Organic sulfoxy compound containing
    • Y10S516/04—Protein or carboxylic compound containing

Definitions

  • Patented Apr.. 24, 1934 STATES UNITE PATENT OFFICE Edward Pohl, Great Neck, N. Y., assignor to Selma Pohl, Great Neck, N. Y.
  • This invention relates to the manufacture of water-soluble oils from vegetable and animal oils and fats which are capable of being sulphonated. These water-soluble oils are adapted for a great variety of uses but primarily for use in various treatments of fibrous or textile materials, such as dyeing and finishing of piece goods, and lubricating the fibres for throwing and weaving.
  • oils and fats contain free fatty acids of high molecular weight and esters of these acids, especially the glycerides. These oils in their natural state are unsuitable for use in the various textile treatments under consideration for the reason that they are not capable of impregnating the material undergoing the treatment, being largely immiscible with water. It is therefore customary to subject these oils to a treatment which will convert them into a watermiscible form.
  • these vegetable and animal oils were converted into water-miscible form by the treatment known as sulphonation.
  • This treatment usually consists of three stages. In the first stage, the oil is acidulated with a predetermined quantity of a concentrated sulphuric acid, usually slightly in excess of the quantity required for sulphonation, at a temperature of about 85 F., for a length of time sufiicient to effect complete sulphonation. In the second stage, the sulphonated oil is washed with a water solution of sodium sulphate, (Glaubers salt) or a substance whose water solution has an alkaline reaction to remove the excess of mineral acid and to stop further conversion of the fat-s into hydroxy fatty acid.
  • sodium sulphate (Glaubers salt) or a substance whose water solution has an alkaline reaction to remove the excess of mineral acid and to stop further conversion of the fat-s into hydroxy fatty acid.
  • This washing l is effected by thoroughly mixing the Water solution of the salt with the acidulated oil.
  • the mixture of salt solution and oil is then allowed to stand until it separates into two layers, the upper layer being the acidulated or sulphonated oil.
  • the lower layer is drawn ofi in a third stage of the process and the remaining oil is treated with a suitable alkali. such as caustic soda, caustic potash or ammonium hydroxide. This treatment neutralizes any remaining free mineral acid, also clears the oil, and reduces the content of free fatty acid to the desired percentage for each particular case.
  • glycerine can be readily combined with the sulphonated oil in the presence of a small amount of free mineral acid.
  • the sulphuric acid used in the sulphonation is highly efiective in this capacity.
  • the action of the sulphuric acid is not completely understood, but it is presumed that it acts as a carrier or a catalyst.
  • the sulphonated oil after the second stage of the sulphonation usually contains a small quantity of free sulphuric acid. In practice, this free acid is neutralized by the treatment with alkali in the third or final stage of that process.
  • glycerine be added to the sulphonated oil after the second stage of the sulphonation process, while there is a quantity of free sulphuric acid present, the glycerine will readily combine with the sulphonated oil to form glycerides. In the event that the free mineral acid is 'completely washed out in the second stage, it is necessary to add a small quantity of free mineral acid together with the glycerine in order to effect the reaction. Likewise, if the glycerine is not added at such a stage of the sulphonation process in which some free mineral acid is present, it is necessary to add a small quantity of free mineral acid with the glycerine. The best results are obtained by using sulphuric acid having a specific gravity of 66 Baum. It is important to immediately neutralize the free acid after the combination of the glycerine with the sulphonated oil is completed,
  • the amount of free mineral acid which must be present during the esterifying of the sulphonated oil with glycerine will vary with the amount of glycerine to be incorporated in the oil.
  • the presence of a large amount of glycerides in the oils will cause fibers treated therewith to swell up. This action is particularly noticeable in artificial fibers.
  • My invention can be appliedto any animal and vegetable oil or fat, such as neats-foot oil, fish oils, liver oils, blubber oils, olive oil, castor oil, cotton-seed oil, palm oil, beef tallow, mutton tallow, etc. or mixtures thereof. While ,my invention is primarily directed to those oils and fats which are capable of being sulphonated, I also contemplate mixing with such oils and fats other oils or fats, which are not of themselves susceptible to sulphonation. For example, cocoanut .oil can be mixed with a sulphonated castor, oil and the mixture can be treated in accordance with my invention.
  • Example 2 One part of ethylene glycol is added to four parts of sulphonated olive oil containing of one percent of 66 Baum sulphuric acid. As soon as the glycol is taken up by the sulphonated oil sufllcient alkali is added to neutralize the acid.
  • Example 3 One part of glycerine is added to four parts of sulphonated neat's-foot oil containing of one percent or more of 66 Baum sulphuric acid. As soon as the oil acquires a brilliant appearance reaction is finished. The reaction mixture is then immediately treated with an alkali substance in .order to neutralize the sulphuric acid present.
  • glycerine is added to four parts of sulphonated whale oil containing of one percent or more of 66 Baum sulphuric acid. As soon as the oil acquires the desired appearance reaction is finished.
  • the reaction mixture is parts of su'lphonate then immediately treated with an alkali substance in order to neutralize the. sulphuric acid present.
  • Example 5 One part of glycerine is added to nine parts of sulphonated tallow containing of one percent or more of 66 Baum sulphuric acid. As soon as the oil acquires the desired appearance the reaction is finished. The reaction mixture is then immediately treated with an alkali substance in order to neutralize the sulphuric acid present.
  • Example 6 of one percent or more of 66 Baum sulphuric acid. As soon as'the oil acquires the desired appearance reaction is finished. The reaction mixture is then immediately treated with an alkali substance in order to neutralize the sulphuric acid present.
  • Example 7 One part of ethylene glycol is added to nine parts of sulphonated whale oil containing of one percent or more of 66 Baum sulphuric acid. As soon as the oil acquires the desired appearance reaction is finished. The reaction mixture is then immediately treated with an alkali substance in order to neutralize the sulphuric acid present.
  • Example 8 One part of manni l is added to four or more castor oil containing of one percent of 66 Baum sulphuric acid. If the acid is not already present, it must be added. After the mixture is stirred for a short time, the mannitol'iscompletely taken up by the sulphonated castor oil. The termination of the reaction is evidenced by the brilliance or uniform appearance which is imparted to the sulphonated oil which of itself presents a rather murky appearance. Suflicienkalkaliis added to neutralize the free acid. The product can be diluted with water to any desired consistency.
  • Example 9 One part of sorbitol is added to nine parts of suphonated castor oil containing of one percent or more of 66 Baum sulphuric acid. If the acid is not already present, it must be added. After the mixture is stirred for ashort time, the sorbitol is completely taken up by the sulphonated castor oil. The termination of the reaction is evidenced by the desired appearance or brilliance which is imparted to the sulphonated oil which of itself presents a rather murky appearance. Suiflcient alkali is added to neutralize the free acid. The product can be diluted with water to any desired consistency.
  • Example 10 One part of mannitol is added to nine parts of sulphonated neats-foot oil containing of one percent or more of 66 Baum sulphuric acid. As soon as the oil acquires the desired appearance reaction is finished. The reaction mixture is then immediately treated with an alkali substance in order to neutral'me the sulphuric acid present.
  • the process of producing an agent for the treatment of textile materials which comprises sulphonating a substance selected from the group consisting of vegetable and animal oils and fats capable of sulphonation and reacting the sulphonation product in the presence of free sulphuric acid with a polyhydric alcohol in an amount; at least sufficient to restore to said product the percentage of combined polyhydric alcohol contained in the oils and fats before sulphonation, stirring the mixture until the sulphonated substance presents a brilliant appearance and then neutralizing the free acid.

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  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

Patented Apr.. 24, 1934 STATES UNITE PATENT OFFICE Edward Pohl, Great Neck, N. Y., assignor to Selma Pohl, Great Neck, N. Y.
No Drawing.
20 Claims.
This invention relates to the manufacture of water-soluble oils from vegetable and animal oils and fats which are capable of being sulphonated. These water-soluble oils are adapted for a great variety of uses but primarily for use in various treatments of fibrous or textile materials, such as dyeing and finishing of piece goods, and lubricating the fibres for throwing and weaving.
These vegetable and animals oils and fats contain free fatty acids of high molecular weight and esters of these acids, especially the glycerides. These oils in their natural state are unsuitable for use in the various textile treatments under consideration for the reason that they are not capable of impregnating the material undergoing the treatment, being largely immiscible with water. It is therefore customary to subject these oils to a treatment which will convert them into a watermiscible form.
Hitherto, these vegetable and animal oils were converted into water-miscible form by the treatment known as sulphonation. This treatment usually consists of three stages. In the first stage, the oil is acidulated with a predetermined quantity of a concentrated sulphuric acid, usually slightly in excess of the quantity required for sulphonation, at a temperature of about 85 F., for a length of time sufiicient to effect complete sulphonation. In the second stage, the sulphonated oil is washed with a water solution of sodium sulphate, (Glaubers salt) or a substance whose water solution has an alkaline reaction to remove the excess of mineral acid and to stop further conversion of the fat-s into hydroxy fatty acid. This washing l is effected by thoroughly mixing the Water solution of the salt with the acidulated oil. The mixture of salt solution and oil is then allowed to stand until it separates into two layers, the upper layer being the acidulated or sulphonated oil. The lower layer is drawn ofi in a third stage of the process and the remaining oil is treated with a suitable alkali. such as caustic soda, caustic potash or ammonium hydroxide. This treatment neutralizes any remaining free mineral acid, also clears the oil, and reduces the content of free fatty acid to the desired percentage for each particular case.
This sulphonation treatment of the natural oil removes therefrom either entirely or substantially 0 entirely the glycerides which were originally present in-the natural oil. If the glycerides could be retained in the processed or water-miscible oils or kept as nearly intact as nature provides them in the natural oil, the resulting product would impart to textile materials treatec therewith in Application October 30, 1931, Serial No. 572,225 7,
dyeing, finishing, throwing or weaving processes, a greater amount of fullness, brilliancy and softness. Moreover, these improved results would be achieved by a smaller quantity of such product than is now used in the achievement of inferior results.
It is an object of my invention to restore to the processed oil or fat all of the original, combined glycerine and to even increase the quantity of combined glycerine, if desired.
Hitherto it has been deemed impossible to esterify the free fatty acids of high molecular weight, such as are contained in animal and vegetable oils, with glycerine in a practical manner. The mere addition of glycerine to the textile treating bath containing the sulphonated oil would not bring about the desired result for the reason that the glycerine would not be uniformly distributed throughout the bath and would lead to the production of a non-uniform product. Consequently, the glycerine must be chemically combined with the sulphonated oil in order to impart to the material under treatment the beneficial properties listed above.
I have found that glycerine can be readily combined with the sulphonated oil in the presence of a small amount of free mineral acid. The sulphuric acid used in the sulphonation is highly efiective in this capacity. The action of the sulphuric acid is not completely understood, but it is presumed that it acts as a carrier or a catalyst. As stated above, the sulphonated oil after the second stage of the sulphonation usually contains a small quantity of free sulphuric acid. In practice, this free acid is neutralized by the treatment with alkali in the third or final stage of that process. If glycerine be added to the sulphonated oil after the second stage of the sulphonation process, while there is a quantity of free sulphuric acid present, the glycerine will readily combine with the sulphonated oil to form glycerides. In the event that the free mineral acid is 'completely washed out in the second stage, it is necessary to add a small quantity of free mineral acid together with the glycerine in order to effect the reaction. Likewise, if the glycerine is not added at such a stage of the sulphonation process in which some free mineral acid is present, it is necessary to add a small quantity of free mineral acid with the glycerine. The best results are obtained by using sulphuric acid having a specific gravity of 66 Baum. It is important to immediately neutralize the free acid after the combination of the glycerine with the sulphonated oil is completed,
The amount of free mineral acid which must be present during the esterifying of the sulphonated oil with glycerine will vary with the amount of glycerine to be incorporated in the oil. The presence of a large amount of glycerides in the oils will cause fibers treated therewith to swell up. This action is particularly noticeable in artificial fibers. Other polyhydric alcohols, such as the various glycols, including ethylene glycol, propylene glycol, butylene glycol and the like, erythritol, mannitol, sorbitol, dulcitol, etc., exert a similar favorable action on textile materials when combined with sulphonated oil in the manner described above.
My invention can be appliedto any animal and vegetable oil or fat, such as neats-foot oil, fish oils, liver oils, blubber oils, olive oil, castor oil, cotton-seed oil, palm oil, beef tallow, mutton tallow, etc. or mixtures thereof. While ,my invention is primarily directed to those oils and fats which are capable of being sulphonated, I also contemplate mixing with such oils and fats other oils or fats, which are not of themselves susceptible to sulphonation. For example, cocoanut .oil can be mixed with a sulphonated castor, oil and the mixture can be treated in accordance with my invention.
The following examples are given to illustrate practical embodiments of my invention, but are in no way to be taken as indicative of the scope thereof.
- Example 1 Example 2 One part of ethylene glycol is added to four parts of sulphonated olive oil containing of one percent of 66 Baum sulphuric acid. As soon as the glycol is taken up by the sulphonated oil sufllcient alkali is added to neutralize the acid.
Example 3 One part of glycerine is added to four parts of sulphonated neat's-foot oil containing of one percent or more of 66 Baum sulphuric acid. As soon as the oil acquires a brilliant appearance reaction is finished. The reaction mixture is then immediately treated with an alkali substance in .order to neutralize the sulphuric acid present.
Example .4
One part of glycerine is added to four parts of sulphonated whale oil containing of one percent or more of 66 Baum sulphuric acid. As soon as the oil acquires the desired appearance reaction is finished. The reaction mixture is parts of su'lphonate then immediately treated with an alkali substance in order to neutralize the. sulphuric acid present.
Example 5 One part of glycerine is added to nine parts of sulphonated tallow containing of one percent or more of 66 Baum sulphuric acid. As soon as the oil acquires the desired appearance the reaction is finished. The reaction mixture is then immediately treated with an alkali substance in order to neutralize the sulphuric acid present.
Example 6 of one percent or more of 66 Baum sulphuric acid. As soon as'the oil acquires the desired appearance reaction is finished. The reaction mixture is then immediately treated with an alkali substance in order to neutralize the sulphuric acid present.
"Example 7 One part of ethylene glycol is added to nine parts of sulphonated whale oil containing of one percent or more of 66 Baum sulphuric acid. As soon as the oil acquires the desired appearance reaction is finished. The reaction mixture is then immediately treated with an alkali substance in order to neutralize the sulphuric acid present.
Example 8 One part of manni l is added to four or more castor oil containing of one percent of 66 Baum sulphuric acid. If the acid is not already present, it must be added. After the mixture is stirred for a short time, the mannitol'iscompletely taken up by the sulphonated castor oil. The termination of the reaction is evidenced by the brilliance or uniform appearance which is imparted to the sulphonated oil which of itself presents a rather murky appearance. Suflicienkalkaliis added to neutralize the free acid. The product can be diluted with water to any desired consistency.
Example 9 One part of sorbitol is added to nine parts of suphonated castor oil containing of one percent or more of 66 Baum sulphuric acid. If the acid is not already present, it must be added. After the mixture is stirred for ashort time, the sorbitol is completely taken up by the sulphonated castor oil. The termination of the reaction is evidenced by the desired appearance or brilliance which is imparted to the sulphonated oil which of itself presents a rather murky appearance. Suiflcient alkali is added to neutralize the free acid. The product can be diluted with water to any desired consistency.
Example 10 One part of mannitol is added to nine parts of sulphonated neats-foot oil containing of one percent or more of 66 Baum sulphuric acid. As soon as the oil acquires the desired appearance reaction is finished. The reaction mixture is then immediately treated with an alkali substance in order to neutral'me the sulphuric acid present.
It will be understood, with reference to all the foregoing examples, that if suflicient combined alkali is present in the product for absorption of the mineral acid, no further alkali need be added.
What I claim as new and desire to secure by Letters Patent is:-
1. The process of producing an agent for the treatment of textile materials which comprises reacting a substance selected from the group consisting of sulphonated vegetable and animal oils and fats in the presence of free sulphuric acid, with a polyhydric alcohol in an amount at least sufficient to restore to said substance the percentage of combined polyhydric alcohol contained in the oils and fats before sulphonation.
2. The process of producing an agent for the treatment of textile materials which comprises sulphonating a substance selected from the group consisting of vegetable and animal oils and fats capable of sulphonation and reacting the sulphonation'product in the presence of free sulphuric acid with a polyhydric "alcohol in an amount at leastsufiicient to restore to said product the percentage of combined polyhydric alcohol contained in the oils and fats before sulphonation.
3. The process of producing an agent for the treatment of textile materials which comprises sulphonating a substance selected from the group consisting of vegetable and animal oils and fats capable of sulphonation and reacting the sulphonation product in the presence of free sul phuric acid with glycerine in 'an amount at least sufficient to restore to said product the percentage of combined glycerine contained in the oils and fats before sulphonation.
4. The process of producing an agent for the treatment of textile materials which comprises reacting a substance selected from the group con sisting of sulphonated vegetable and animal oils and fats in the presence of free sulphuric acid with glycerine in an amount at least sufficient to restore to said substance the percentage of combined glycerine contained in the oils and fats before sulphonation.
5. The process of producing an agent for the treatment of textile materials which comprises reacting sulphonated castor oil in the presence of free sulphuric acid with a polyhydric alcohol in an amount at least sufficient to restore to said sulphonated oil the percentage of combined polyhydric alcohol contained in the oil before sulphonation.
6. The process of producing an agent for the treatment of textile materials which comprises reacting sulphonated olive oil in the presence of free sulphuric acid with a polyhydric alcohol in an amount at least sufficient to restore to said sulphonated oil the percentage of combined polyhydric alcohol contained in the oil before sulphonation.
7. The process of producing an agent for the treatment of textile materials which comprises reacting sulphonated castor oil in the presence of free sulphuric acid with glycerine in an amount at least sufiicient to restore to said sulphonated oil the percentage of combined polyhydric alcohol contained in the oil before sulphonation.
8. The process of producing an agent for the treatment of textile materials which comprises reacting glycerine with sulphonated olive oil in phonation.
9. The process of producing an agent for the treatment of textile materials which comprises reacting a substance selected from the group consisting of sulphonated vegetable and animal oils and fats in the presence of free sulphuric acid with ethylene glycol in an amount atleast sufficient to restore to said substance the percentage of combined polyhydric alcohol contained in the oils and fats before sulphonation.
10. The process of producing an agent for the treatment of textile materials which comprises sulphonating a substance selected from the group consisting of vegetable and animal oils and fats capable of sulphonation and reacting the sulphonation product in the presence of free sulphuric acid with ethylene glycol in an amount at least sufiicient to restore to said sulphonated product the percentage of combined polyhydric alcohol contained in the oils and fats before sulphonation.
11. The process of producing an agent for the treatment of textile materials which comprises reacting sulphonated castor oil in the presence of free sulphuric acid with ethylene glycol in an amount at least sufficient to restore to said sulphonated oil the percentage of combined polyhydric alcohol contained in the oil before sulphonation.
12. The process of producing an agent for the treatment of textile materials which comprises reacting sulphonated olive oil in the presence of free sulphuric acid with ethylene glycol in an amount at least sufiicient to restore to said sulphonated oil the percentage of combined polyhydric alcohol contained in the oil before sulphonation.
13. The process of producing an agent for the treatment of textile materials which comprises reacting a substance selected from the group consisting of sulphonated vegetable and animal oils and fatsin the presence of free sulphuric acid with a polyhydric alcohol in an amount at least sufficient to restore to said substance the percentage of combined polyhydric alcohol contained in the oils and fats before sulphonation, stirring the mixture until the sulphonated substance presents a brilliantappearance and then neutralizing,
the free acid.
14. The process of producing an agent for the treatment of textile materials which comprises sulphonating a substance selected from the group consisting of vegetable and animal oils and fats capable of sulphonation and reacting the sulphonation product in the presence of free sulphuric acid with a polyhydric alcohol in an amount; at least sufficient to restore to said product the percentage of combined polyhydric alcohol contained in the oils and fats before sulphonation, stirring the mixture until the sulphonated substance presents a brilliant appearance and then neutralizing the free acid.
15. The process of producing an agent for the treatment of textile materials which comprises reacting sulphonated castor oil in the presence of free sulphuric acid with a polyhydric alcohol in an amount at least suflicient to restoreto said sulphonated oil the percentage of combined polyhydric alcohol contained in the castor oil before sulphonation, stirring the mixture until the sulphonated substance presents a brilliant appearance and then neutralizing the free acid.
16. The process of producing an agent for the treatment of textile materials which comprises reacting sulphonated castor oil in the presence of free sulphuric acid with glycerine in an amount at least sufiicient to restore to said sulphonated oil the percentage of combined glycerine contained in the castor oil before sulphonation, stirof combined polyhydric alcohol contained in the oils and fats before sulphonation, stirring the mixture until the sulphonated substance presents a brilliant appearance and then neutralizing the free acid.
18. The process of producing an agent for the treatment of textile materials which comprises reacting sulphonated olive oil in the presence of free sulphuric acid with ethylene glycol in an amount at least suflicient to restore to said oil the percentage of combined polyhydric alcohol conta ned in the olive oil before sulphonation, stirring the mixture until the sulphonated substance presents a brilliant appearance and then neutralizing the free acid. a
19. The product of the process of claim 1.
20. The product of the process of claim '7.
' EDWARD POI-IL.
US572225A 1931-10-30 1931-10-30 Manufacture of sulphonated oils Expired - Lifetime US1955766A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3167446A (en) * 1961-03-08 1965-01-26 Lederfabriek L Mombers Nv Coated textile materials and process

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3167446A (en) * 1961-03-08 1965-01-26 Lederfabriek L Mombers Nv Coated textile materials and process

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